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Full text of "Practical Organic Chemistry"

3io

PRACTICAL  ORGANIC  CHEMISTRY

(3) With an aromatic hydrocarbon and a halogen derivative
of an aliphatic hydrocarbon or aromatic hydrocarbon .substi-
tuted in the side-chain, new hydrocarbons may be built up (see
Prep. 102, p. 214),

QI-I,. + CoIIr,Br = C,;Hfi.C2H, + IIBr.

Ktliylben/ene.

C8H6 + ClCHo.CV.IIn ~ C,iII5.CII2.C,sHB + MCI,

Diphenylmethane.

3CfiHG + CI1C13 = CH(C(;II,)., + slid.

Triphenylinethane.

Anthracene has been, synthesised from tetrabromethane and
benzene by this method,

I      Br ! CII ! Hr      !                             ,CIU

CVIL; 11.,    i !    ;    iio:c(iii4 = ctin/ i   X,c(in4 + 4iiBr.

'     ;     ~Hr ! CII    Ur    "i                             '

Anthracene.

(4)  Amides may be prepared by the use of chloroformamide,

CBH0 -I- CICONHo = CGHVCO.NH3 + ITC1.

The chloroformamide is obtained by passing HC1 gas over
heated cyanuric acid (Gattermann),

IIOCN + 1IC1 = Cl.CONIIo.

(5)   Hydroxyaldehydes have been obtained indirectly by -the
use of the crystalline compound HCI.HCN (which hydrochloric
acid forms with hydrocyanic acid) acting upon a phenol ether,

Cfln,OCH8 + HCI.HCN =

/OCH3
SCH:NH.

The aldime is subsequently hydrolysed  with dilute sulphuric
acid (Gattermann),

H20   =   C0H4<
\

NIL,

COH

In   addition  to  the   Friedel-Crafts' reaction,   the  aromatic
ketones may be obtained by distilling the calcium salt of the